Potassium Hydroxide → 2-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionic acid

HRID 274046Notes

Reaction equation

HRID 274046 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:21].Cl[C:23](Cl)(Cl)[C:24]([CH3:27])(O)[CH3:25].[OH-:30].[K+]>CC(C)=O>[CH2:1]([NH:8][CH:9]1[CH2:15][C:14]2[CH:16]=[C:17]([O:20][C:24]([CH3:27])([CH3:25])[C:23]([OH:30])=[O:21])[CH:18]=[CH:19][C:13]=2[CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 122198322-Propanol, 1,1,1-trichloro-2-methyl-, hydrateHCID 18007284HCID 18007284, compound

Product 1

HCID 200947372-(8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)-2-methylpropionic acidYield 39.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (970 mg) and 1,1,1-trichloro-2-methyl-2-propanol hydrate (1.28 g) in acetone (30 ml) was added portionwise powder KOH (1.71 g) and the mixture was stirred for 20 hours at ambient temperature. After the solvent was evaporated in vacuo, the residue was poured into 1N sodium hydroxide (30 ml) and washed with diethyl ether. The pH of the aqueous layer was adjusted to 6.0 with 3N hydrochloric acid. The precipitates were filtered off. The filtrate was concentrated in vacuo and water was added to the residue. The resulting precipitates were collected by filtration and dried to give 2-[8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-2-methylpropionic acid (0.51 g).

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. additionthe residue was poured into 1N sodium hydroxide (30 ml)
  3. washwashed with diethyl ether
  4. filtrationThe precipitates were filtered off
  5. concentrationThe filtrate was concentrated in vacuo and water
  6. additionwas added to the residue
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-74828932c7fb4ca9b27ccec206303d0d
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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